1H-Pyrazole-3-carboxylic acid, 4-nitro-, methyl ester
- Product Name
- 1H-Pyrazole-3-carboxylic acid, 4-nitro-, methyl ester
- CAS No.
- 138786-86-4
- Chemical Name
- 1H-Pyrazole-3-carboxylic acid, 4-nitro-, methyl ester
- Synonyms
- 3-Methoxycarbonyl-4-nitropyrazole;Methyl 4-Nitropyrazole-3-carboxylate;Methyl 4-nitro-1H-pyrazol-3-carboxylate;methyl 4-nitro-4H-pyrazole-3-carboxylate;methyl 4-nitro-2H-pyrazole-3-carboxylate;4-Nitropyrazole-3-carboxylic acid methyl ester;4-Nitro-1H-pyrazole-3-carboxylic acid Methyl ester;1H-PYRAZOLE-5-CARBOXYLIC ACID 4-NITRO- METHYL ESTER;1H-Pyrazole-3-carboxylic acid, 4-nitro-, methyl ester;4-nitro-1H-Pyrazole-3-carboxylic acid methyl ester (9CI ACI)
- CBNumber
- CB61509207
- Molecular Formula
- C5H5N3O4
- Formula Weight
- 171.11
- MOL File
- 138786-86-4.mol
1H-Pyrazole-3-carboxylic acid, 4-nitro-, methyl ester Property
- Boiling point:
- 363.2±22.0 °C(Predicted)
- Density
- 1.545
- storage temp.
- 2-8°C
- pka
- 6.67±0.50(Predicted)
- form
- solid
- color
- Off-white to light yellow
- InChI
- InChI=1S/C5H5N3O4/c1-12-5(9)4-3(8(10)11)2-6-7-4/h2H,1H3,(H,6,7)
- InChIKey
- ARAFBUCGMOKZMI-UHFFFAOYSA-N
- SMILES
- N1C=C([N+]([O-])=O)C(C(OC)=O)=N1
Safety
- HazardClass
- IRRITANT
- HS Code
- 2933199090
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P271Use only outdoors or in a well-ventilated area.
P280Wear protective gloves/protective clothing/eye protection/face protection.
N-Bromosuccinimide Price
- Product number
- M339143
- Product name
- Methyl4-Nitro-1H-pyrazole-3-carboxylate
- Packaging
- 50mg
- Price
- $45
- Updated
- 2021/12/16
- Product number
- 113995
- Product name
- Methyl 4-nitro-1H-pyrazole-3-carboxylate
- Purity
- 97%
- Packaging
- 1g
- Price
- $15
- Updated
- 2021/12/16
- Product number
- X0355
- Product name
- Methyl4-nitro-1H-pyrazole-3-carboxylate
- Packaging
- 1g
- Price
- $21
- Updated
- 2021/12/16
- Product number
- J94817
- Product name
- Methyl4-nitro-1H-pyrazole-3-carboxylate
- Packaging
- 5g
- Price
- $45
- Updated
- 2021/12/16
- Product number
- X0355
- Product name
- Methyl4-nitro-1H-pyrazole-3-carboxylate
- Packaging
- 5g
- Price
- $61
- Updated
- 2021/12/16
1H-Pyrazole-3-carboxylic acid, 4-nitro-, methyl ester Chemical Properties,Usage,Production
Synthesis
67-56-1
5334-40-7
138786-86-4
4-Nitro-1H-pyrazole-3-carboxylic acid (1.117 kg, 7.11 mol, 1.0 equiv.) and methanol (8.950 L, 8.0 v/v) were added to a 20 L reactor equipped with a digital thermometer and a mechanical stirrer. The reaction mixture was cooled to 0-5 °C under nitrogen protection and thionyl chloride (0.581 L, 7.96 mol, 0.52 v/v) was slowly added dropwise over 180 min. After the dropwise addition, the reaction mixture was gradually warmed to 18-25 °C and stirred overnight. After confirming the completion of the reaction by 1H NMR (d6-DMSO), the reaction mixture was concentrated at 40-45 °C under reduced pressure. The residue was treated with toluene (3 x 2.250 L, 3 x 2 v/v) and concentrated under reduced pressure at the same temperature to afford methyl 4-nitro-1H-pyrazole-3-carboxylate as an off-white solid (1.210 kg, 99.5% yield). In another experiment, 4-nitro-1H-pyrazole-3-carboxylic acid (1.00 kg, 6.37 mol, 1.0 eq.) and methanol (8.00 L, 8.0 v/v) were added to a flanged flask fitted with a mechanical stirrer, condenser and thermometer. The suspension was cooled to 0-5 °C under nitrogen protection and thionyl chloride (0.52 L, 7.12 mol, 0.52 v/v) was slowly added at this temperature. The mixture was gradually warmed to 15-25 °C over 16-24 h and the completion of the reaction was confirmed by 1H NMR (d6-DMSO). The reaction mixture was concentrated under reduced pressure at 35-45 °C and the residue was treated with toluene (2.00 L, 2.0 v/v) and the solvent was removed under reduced pressure at the same temperature. This process was repeated twice to give the final methyl 4-nitro-1H-pyrazole-3-carboxylate as an off-white solid (1.071 kg, 98.3% yield). In a small-scale experiment, thionyl chloride (2.90 mL, 39.8 mmol) was slowly added to a methanol (100 mL) solution of 4-nitro-1H-pyrazole-3-carboxylic acid (5.68 g, 36.2 mmol) at room temperature and the mixture was stirred for 48 hours. Upon completion of the reaction, the mixture was concentrated under reduced pressure and residual water was removed by azeotropy with toluene to afford methyl 4-nitro-1H-pyrazole-3-carboxylate as a white solid.1H NMR (400 MHz, DMSO-d6) δ 14.4 (s, 1H), 8.9 (s, 1H), 3.9 (s, 3H). Finally, 4-nitro-1H-pyrazole-3-carboxylic acid (1.350 kg, 8.59 mol, 1.0 eq.) and methanol (10.80 L, 8.0 v/v) were added to a flanged flask fitted with a mechanical stirrer, condenser and thermometer. The suspension was cooled to 0-5 °C under nitrogen protection and thionyl chloride (0.702 L, 9.62 mol, 0.52 v/v) was slowly added at this temperature. The mixture was gradually warmed to 15-25 °C over 16-24 h and the completion of the reaction was confirmed by 1H NMR (d6-DMSO). The reaction mixture was concentrated under reduced pressure at 35-45 °C and the residue was treated with toluene (2.70 L, 2.0 v/v) and the solvent was removed under reduced pressure at the same temperature. This procedure was repeated twice to give methyl 4-nitro-1H-pyrazole-3-carboxylate as an off-white solid (1.467 kg, 99.8% yield).1H NMR (d6-DMSO) was consistent with the structure and no entrapped solvent was detected.
References
[1] Patent: US2009/156582, 2009, A1. Location in patent: Page/Page column 28
[2] Patent: EP1847531, 2007, A1. Location in patent: Page/Page column 40
[3] ACS Medicinal Chemistry Letters, 2013, vol. 4, # 10, p. 979 - 984
[4] Patent: CN107652293, 2018, A. Location in patent: Paragraph 0099; 0100; 0101
[5] Patent: WO2006/77426, 2006, A2. Location in patent: Page/Page column 71-73; 96-97
1H-Pyrazole-3-carboxylic acid, 4-nitro-, methyl ester Preparation Products And Raw materials
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View Lastest Price from 1H-Pyrazole-3-carboxylic acid, 4-nitro-, methyl ester manufacturers
- Product
- Methyl 4-nitro-1h-pyrazole-3-carboxylate 138786-86-4
- Price
- US $0.00/KG
- Min. Order
- 1KG
- Purity
- 98.2%
- Supply Ability
- 100 tons
- Release date
- 2022-01-26
- Product
- 1H-Pyrazole-3-carboxylic acid, 4-nitro-, methyl ester 138786-86-4
- Price
- US $1.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- 200KG
- Release date
- 2018-12-23